Pyryliumolates II - Generation of and cycloaddition reactions with isoxazole annulated pyryliumolates

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 10, 1996, Pages 1035-1040

  Plüg, Carsten ^a   Friedrichsen, Willy ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542420444     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960001035     Document Type: Article

References (69)

1. Pyryliumolates I: C. Plüg and W. Friedrichsen, Tetrahedron Lett., 1992, 33, 7509.
2. (a) E. Ciganek, Org. React., 1984, 32, 1;
3. (b) A. G. Fallis, Can. J. Chem., 1984, 62, 183;
4. (c) D. Craig, Chem. Soc. Rev., 1987, 16, 187;
5. (d) W. R. Roush, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 1, p. 513.
6. (a) B. A. Keay and R. Rodrigo, J. Am. Chem. Soc., 1982, 104, 4725;
7. (b) B.-M. König and W. Friedrichsen, Tetrahedron Lett., 1987, 28, 4279;
8. (c) W. Friedrichsen, B.-M. König, K. Hildebrandt and T. Debaerdemaeker, Heterocycles, 1986, 24, 297;
9. (d) K. Hildebrandt, T. Debaerdemaeker and W. Friedrichsen, Tetrahedron Lett., 1988, 29, 2045;
10. (e) L. Aßmann, T. Debaerdemaeker and W. Friedrichsen, Tetrahedron Lett., 1991, 32, 1161;
11. (f) J. Nagel, W. Friedrichsen and T. Debaerdemaeker, Z. Naturforsch., Teil B, 1993, 48, 213.
12. (a) W. Friedrichsen, Adv. Heterocycl. Chem., 1980, 26, 135;
13. (b) R. Rodrigo, Tetrahedron, 1988, 44, 2093;
14. (c) B. Rickborn, in Adv. Theoretically Interset. Molecules, ed. R. P. Thummel, 1989, JAI Press, Greenwich, Conn., 1989, vol. 1, p. 1;
15. (d) W. Friedrichsen, in Houben-Weyl, Methoden der Organischen Chemie, ed. R. Kreher, Thieme Verlag, Stuttgart, 1994, vol. E6b1, p. 163.
16. 6a that on heating a solution of 2,3-diphenylindenone epoxide generates a red colour. These authors did not give an explanation for this phenomenon.
17. (a) E. Weitz and A. Scheffer, Ber. Dtsch. Chem. Ges., 1921, 54, 2327;
18. (b) E. F. Ullman and W. A. Henderson, J. Am. Chem. Soc., 1966, 88, 4942;
19. (c) K. Ueda, T. Ibata and M. Takebayashi, Bull. Chem. Soc. Jpn., 1972, 45, 2779;
20. (d) W. Friedrichsen, W. Seidel and T. Debaerdemaeker, J. Heterocycl. Chem., 1983, 20, 1621;
21. (e) K. S. Feldman, Tetrahedron Lett., 1983, 29, 5585;
22. (f) V. M. Zolin, N. D. Dmitrieva, Y. E. Gerasimenko and A. V. Zubkov, Khim. Geterotsikl. Soedin., 1984, 167
23. (Chem. Abstr., 1984, 101, 6338);
24. (g) A. Padwa, S. P. Carter and H. J. Nimmesgern, J. Org. Chem., 1986, 51, 1157;
25. (h) P. G. Sammes, Gazz. Chim. Ital., 1986, 116, 109;
26. (i) A. Padwa, S. P. Carter, H. J. Nimmesgern and P. D. Stull, J. Am. Chem. Soc., 1988, 110, 2894;
27. (j) A. R. Katritzky and N. Dennis, Chem. Rev., 1989, 89, 827;
28. (k) A. Lupi, M. Patomia and F. Arcamone, Gazz. Chim. Ital. 1990, 120, 277;
29. (l) P. A. Wender and J. L. Mascarenas, J. Org. Chem., 1991, 56, 6267;
30. (m) A. Padwa and K. E. Krumpe, Tetrahedron, 1992, 48, 5385;
31. (n) B. J. McBride and M. E. Garst, Tetrahedron, 1993, 49, 2839;
32. (o) A. Padwa, J. Chin. Chem. Soc., 1993, 40, 97;
33. (p) K. Matsumoto, Y. Ikemi, M. Toda, A. Kakehi, T. Uchida and J. W. Lown, Tetrahedron Lett., 1995, 36, 3011;
34. (q) K. Matsumoto, Y. Ikemi, A. Kakehi, A. Shigihara and J. W. Lown, Tetrahedron Lett., 1995, 36, 5295.
35. 8
36. (a) K. Ueda, T. Ibata and M. Takebayashi, Bull. Chem. Soc. Jpn., 1972, 45, 2779;
37. (b) T. Ibata, T. Motoyama and M. Hamaguchi, Bull. Chem. Soc. Jpn., 1976, 49, 2298;
38. (c) T. Ibata, Chem. Lett., 1976, 233;
39. (d) T. Ibata and K. Jitsuhiro, Bull. Chem. Soc. Jpn., 1979, 52, 3582;
40. (e) T. Ibata, K. Jitsuhiro and Y. Tsubokura, Bull. Chem. Soc. Jpn., 1981, 54, 240;
41. (f) T. Ibata and J. Toyoda, Chem. Lett., 1983, 1453-1456;
42. (g) H. Tamur, T. Ibata and K. Ogawa, Bull. Chem. Soc. Jpn., 1984, 57, 926;
43. (h) J. Toyoda, T. Ibata, H. Tamura, K. Ogawa, T. Nishino and M. Takebayashi, Bull. Chem. Soc. Jpn., 1985, 58, 2212;
44. (i) T. Ibata, H. Nakamo and H. Tamura, Bull. Chem. Soc. Jpn., 1986, 59, 2489;
45. (j) T. Ibata, J. Toyoda, M. Sawada, Y. Takai and T. Tanaka, J. Chem. Soc., Chem. Commun., 1986, 1266;
46. (k) T. Ibata, J. Tojoda, M. Sawada, Y. Takai and T. Tonaka, Tetrahedron Lett., 1988, 29, 317;
47. (l) T. Ibata, H. Nakamo and H. Tamura, Bull. Chem. Soc. Jpn., 1992, 65, 1362.
48. E. Kaji, K. Horada and S. Zen, Chem. Pharm. Bull., 1978, 28, 3254.
49. 13C NMR spectrum of 5 (vide infra).
50. 12 For the reactions described in this paper dirhodium tetraacetate was found to be superior over others.
51. (a) M. Regitz and G. Maas, Diazo Compounds, Academic Press, Orlando, 1986;
52. (b) G. Maas, Top. Curr. Chem., 1987, 137, 75.
53. A. Nikatschalo, Diploma Thesis, University of Kiel, 1990.
54. Compound 2d has been mentioned in the patent literature: Eur. Pat. Appl. EP 418, 667 (V. Maywald, W. Freund, G. Hamprecht, T. Kuekenhoehner, P. Plath, B. Wuerzer and K. O. Westphalen) (Chem. Abstr., 1991, 115, 92250).
55. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
56. (a) J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209;
57. (b) J. J. P. Stewart, J. Comput. Chem., 1989, 10, 221.
58. Reviews: (a) J. J. P. Stewart, in Reviews in Computational Chemistry, eds. K. B. Lipkowitz and D. B. Boyd, VCH Publishers, New York, 1990;
59. (b) M. C. Zerner, in Reviews in Computational Chemistry, eds. K. B. Lipkowitz and D. B. Boyd, vol. 2, VCH Publishers, New York, 1991.
60. (a) See e.g., R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989;
61. (b) T. Ziegler, Chem. Rev., 1991, 91, 651;
62. (c) J. Baker, M. Muir and J. Andzelm, J. Chem. Phys., 1995, 102, 2063;
63. (d) B. Jursic and Z. Zdaravkovski, J. Chem. Soc., Perkin Trans. 2, 1995, 1223.
64. A. D. Becke, J. Chem. Phys., 1993, 98, 1372.
65. C. Lee, W. Yang and R. G. Parr, Phys. Rev., 1988, 37B, 785.
66. H. Shimanouchi and Y. Sasada, Acta Crystallogr., Sect. B, 1973, 29, 81.
67. For semiempirical studies of compounds with OH-O groups see: M. A. Rios and J. Rodriguez, J. Comput. Chem., 1992, 13, 860.
68. L. A. Brooks and H. R. Snyder, Org. Synth., Coll. Vol., 1955, 3, 698.
69. G. Eglinton, E. H. R. Jones and M. C. Whiting, J. Chem. Soc., 1952, 2873.